CA2203183A1 - Procede de preparation de derives de 4a,5,9,10,11,12,-hexahydro-6h-benzofuro[3a,3,2-ef][2]benzazepine - Google Patents

Procede de preparation de derives de 4a,5,9,10,11,12,-hexahydro-6h-benzofuro[3a,3,2-ef][2]benzazepine

Info

Publication number: CA2203183A1
Authority: CA; Canada
Prior art keywords: galanthamine; bromine; compound; benzofuro; benzazepine
Prior art date: 1994-10-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

CA002203183A

Other languages

English (en)

Other versions

CA2203183C (fr

Inventor

Laszlo Czollner

Johannes Frohlich

Ulrich Jordis

Bernhard Kuenburg

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanochemia Pharmazeutika AG

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-10-21

Filing date

1995-10-23

Publication date

1996-05-02

1994-10-21 Priority claimed from AT198094A external-priority patent/AT401058B/de

1995-10-23 Application filed by Individual filed Critical Individual

1996-05-02 Publication of CA2203183A1 publication Critical patent/CA2203183A1/fr

2008-04-08 Application granted granted Critical

2008-04-08 Publication of CA2203183C publication Critical patent/CA2203183C/fr

2015-10-23 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title abstract 4
DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 title abstract 2
ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 abstract 10
ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 abstract 4
HPOIPOPJGBKXIR-UHFFFAOYSA-N 3,6-dimethoxy-10-methyl-galantham-1-ene Natural products O1C(C(=CC=2)OC)=C3C=2CN(C)CCC23C1CC(OC)C=C2 HPOIPOPJGBKXIR-UHFFFAOYSA-N 0.000 abstract 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
LPCKPBWOSNVCEL-UHFFFAOYSA-N Chlidanthine Natural products O1C(C(=CC=2)O)=C3C=2CN(C)CCC23C1CC(OC)C=C2 LPCKPBWOSNVCEL-UHFFFAOYSA-N 0.000 abstract 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
229910052794 bromium Inorganic materials 0.000 abstract 3
150000001875 compounds Chemical class 0.000 abstract 3
229960003980 galantamine Drugs 0.000 abstract 3
BGLNUNCBNALFOZ-WMLDXEAASA-N galanthamine Natural products COc1ccc2CCCC[C@@]34C=CCC[C@@H]3Oc1c24 BGLNUNCBNALFOZ-WMLDXEAASA-N 0.000 abstract 3
IYVSXSLYJLAZAT-NOLJZWGESA-N lycoramine Natural products CN1CC[C@@]23CC[C@H](O)C[C@@H]2Oc4cccc(C1)c34 IYVSXSLYJLAZAT-NOLJZWGESA-N 0.000 abstract 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
239000002253 acid Substances 0.000 abstract 1
230000015572 biosynthetic process Effects 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 abstract 1
238000010586 diagram Methods 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
230000011987 methylation Effects 0.000 abstract 1
238000007069 methylation reaction Methods 0.000 abstract 1
238000001556 precipitation Methods 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
238000000926 separation method Methods 0.000 abstract 1
229940095064 tartrate Drugs 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Other In-Based Heterocyclic Compounds (AREA)

CA002203183A 1994-10-21 1995-10-23 Procede de preparation de derives de 4a,5,9,10,11,12,-hexahydro-6h-benzofuro[3a,3,2-ef][2]benzazepine Expired - Lifetime CA2203183C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
AT198094A AT401058B (de)	1994-10-21	1994-10-21	Verfahren zum herstellen von derivaten des 4a,5, 9,10,11,12,-hexahydro-6h-benzofuro(3a,-3,2-ef) (2)benzazepins
ATA1980/94		1994-10-21
US48710295A	1995-06-07	1995-06-07
US08/487,102		1995-06-07
PCT/AT1995/000208 WO1996012692A1 (fr)	1994-10-21	1995-10-23	PROCEDE DE PREPARATION DE DERIVES DE 4a,5,9,10,11,12,-HEXAHYDRO-6H-BENZOFURO[3a,3,2-ef][2]BENZAZEPINE

Publications (2)

Publication Number	Publication Date
CA2203183A1 true CA2203183A1 (fr)	1996-05-02
CA2203183C CA2203183C (fr)	2008-04-08

Family

ID=25597335

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002203183A Expired - Lifetime CA2203183C (fr)	1994-10-21	1995-10-23	Procede de preparation de derives de 4a,5,9,10,11,12,-hexahydro-6h-benzofuro[3a,3,2-ef][2]benzazepine

Country Status (27)

Country	Link
US (1)	US6043359A (fr)
EP (1)	EP0787115B1 (fr)
JP (1)	JP4187786B2 (fr)
KR (1)	KR100352212B1 (fr)
CN (1)	CN1069624C (fr)
AT (1)	ATE188460T1 (fr)
AU (1)	AU695352B2 (fr)
BG (1)	BG62133B1 (fr)
BR (1)	BR9509406A (fr)
CA (1)	CA2203183C (fr)
CZ (1)	CZ295528B6 (fr)
DE (1)	DE59507585D1 (fr)
DK (1)	DK0787115T3 (fr)
ES (1)	ES2106700T3 (fr)
FI (1)	FI114477B (fr)
GR (2)	GR980300015T1 (fr)
HU (1)	HU217207B (fr)
MX (1)	MX9702892A (fr)
NO (2)	NO313234B1 (fr)
NZ (1)	NZ294191A (fr)
PL (1)	PL184590B1 (fr)
PT (1)	PT787115E (fr)
RO (1)	RO118419B1 (fr)
RU (1)	RU2146258C1 (fr)
SI (1)	SI0787115T1 (fr)
SK (1)	SK283877B6 (fr)
WO (1)	WO1996012692A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU785385B2 (en) *	2000-03-31	2007-03-29	Sanochemia Pharmazeutika Aktiengesellschaft	Novel derivatives and analogues of galanthamin

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9519267D0 (en) *	1995-09-21	1995-11-22	Chiroscience Ltd	Preparation of alkaloids
AT403803B (de)	1996-04-19	1998-05-25	Sanochemia Ltd	Neue benzazepinderivate, diese enthaltende arzneimittel und verwendung derselben zum herstellen von arzneimitteln
GB9610887D0 (en) *	1996-05-24	1996-07-31	N H S Trust	Process
GB9707413D0 (en) *	1997-04-11	1997-05-28	Chiroscience Ltd	Process
US6897228B2 (en) *	2000-07-07	2005-05-24	Medicure International Inc.	Pyridoxine and pyridoxal analogues: new uses
WO2002061457A2 (fr) *	2001-01-30	2002-08-08	Decharms R Christopher	Procedes de surveillance physiologique, d'entrainement, d'exercice et de regulation
DE10129265A1 (de) *	2001-06-18	2003-01-02	Hf Arzneimittelforsch Gmbh	Wirkstoff-Kombination zur medikamentösen Sucht- oder Rauschmitteltherapie
DE10134038A1 (de) *	2001-07-12	2003-02-06	Hf Arzneimittelforsch Gmbh	Wirkstoff-Kombination zur medikamentösen Therapie der Nikotinabhängigkeit
US20060111341A1 (en) *	2003-09-29	2006-05-25	Angelika Bodenteich	Use of galanthamine and the derivatives thereof in the production of medicaments
AT414125B (de) *	2003-09-29	2006-09-15	Sanochemia Pharmazeutika Ag	Neue derivate des 4a,5,9,10,11,12-hexahydro- benzofuro(3a,3,2)(2) benzazepin, verfahren zu deren herstellung sowie deren verwendung zur herstellung von arzneimitteln
WO2005065662A1 (fr) *	2003-12-31	2005-07-21	Actavis Group Hf	Formulations solides d'administration de galantamine
CA2551946A1 (fr) *	2003-12-31	2005-07-21	Actavis Group Hf	Formulations de galantamine
WO2006013546A2 (fr) *	2004-07-28	2006-02-09	Ranbaxy Laboratories Limited	Procede de preparation de galantamine pure
WO2006018703A2 (fr) *	2004-08-16	2006-02-23	Ranbaxy Laboratories Limited	Procedes de preparation de la narwedine et son utilisation dans la synthese de galantamine
AR054753A1 (es) *	2005-05-03	2007-07-11	Medichem Sa	Sintesis y preparaciones de narwedina galantamina y compuestos relacionados
AT504663B1 (de) *	2007-02-22	2008-07-15	Sanochemia Pharmazeutika Ag	Verfahren zum herstellen von hochreinen 4a,5,9,10,11,12,-hexahydro-6h-benzofuro(3a,3,2- f)(2) benzazepinen sowie dessen derivaten
NZ580271A (en)	2007-04-12	2011-03-31	Scinopharm Taiwan Ltd	Process for making galantamine
EP2009015B1 (fr)	2007-06-18	2012-01-11	Aurobindo Pharma Limited	Procédé pour la préparation de bromhydrate de galantamine
AT507039A1 (de) *	2008-06-26	2010-01-15	Sanochemia Pharmazeutika Ag	Verfahren zum herstellen von hochreinen benzazepinderivaten
DE102008056086A1 (de) *	2008-11-06	2010-05-12	Gp Solar Gmbh	Additiv für alkalische Ätzlösungen, insbesondere für Texturätzlösungen sowie Verfahren zu dessen Herstellung
WO2013160728A1 (fr)	2012-04-26	2013-10-31	Alma Mater Studiorum - Universita' Di Bologna	Composés à double ciblage pour le traitement de la maladie d'alzheimer
CN102924462B (zh) *	2012-10-24	2015-01-14	华东师范大学	1,2,3,4,5,9-取代苯并吖庚因类化合物的合成方法
CN103345954B (zh) *	2013-06-20	2016-06-08	哈尔滨工业大学	一种高锰酸盐与活性炭联用去除放射性碘污染的水处理方法
CN109336897A (zh) *	2018-12-06	2019-02-15	河南中帅医药科技股份有限公司	一种氢溴酸加兰他敏工业化制备方法
CN112521364B (zh) *	2019-09-17	2023-09-05	鲁南制药集团股份有限公司	一种加兰他敏中间体化合物v
CN112521395B (zh) *	2019-09-17	2023-09-05	鲁南制药集团股份有限公司	一种加兰他敏的制备方法
CN110714208B (zh) *	2019-10-30	2020-12-29	常州工学院	一种电催化制备6-(磺酰甲基)菲啶类化合物的方法
CN118908968B (zh) *	2024-10-09	2025-03-04	威胜生物医药(苏州)股份有限公司	一种加兰他敏中间体衍生物及其催化氧化制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BG28325A1 (en) *	1978-11-21	1980-04-15	Vlakhov	Method of obtaining of enons navedine type and their derivatives
US4290862A (en) *	1979-11-14	1981-09-22	Edinen Centar P Chimia	Method for the preparation of narwedine-type enones
US4663318A (en) *	1986-01-15	1987-05-05	Bonnie Davis	Method of treating Alzheimer's disease
EP0363415B1 (fr) *	1987-05-04	2008-10-15	Davis, Bonnie	Composes permettant le traitement de la maladie d'alzheimer
US5428159A (en) *	1994-04-08	1995-06-27	Ciba-Geigy Corporation	Method of manufacture of (-)-galanthamine in high yield and purity substantially free of epigalanthamine

1995
- 1995-10-23 WO PCT/AT1995/000208 patent/WO1996012692A1/fr not_active Ceased
- 1995-10-23 HU HU9800766A patent/HU217207B/hu unknown
- 1995-10-23 RU RU97107848A patent/RU2146258C1/ru active
- 1995-10-23 JP JP51352796A patent/JP4187786B2/ja not_active Expired - Fee Related
- 1995-10-23 AT AT95944807T patent/ATE188460T1/de active
- 1995-10-23 KR KR1019970702612A patent/KR100352212B1/ko not_active Expired - Lifetime
- 1995-10-23 DK DK95944807T patent/DK0787115T3/da active
- 1995-10-23 SI SI9530182T patent/SI0787115T1/xx unknown
- 1995-10-23 CA CA002203183A patent/CA2203183C/fr not_active Expired - Lifetime
- 1995-10-23 SK SK483-97A patent/SK283877B6/sk not_active IP Right Cessation
- 1995-10-23 ES ES95944807T patent/ES2106700T3/es not_active Expired - Lifetime
- 1995-10-23 CZ CZ19971195A patent/CZ295528B6/cs not_active IP Right Cessation
- 1995-10-23 RO RO97-00721A patent/RO118419B1/ro unknown
- 1995-10-23 DE DE59507585T patent/DE59507585D1/de not_active Expired - Lifetime
- 1995-10-23 BR BR9509406A patent/BR9509406A/pt not_active Application Discontinuation
- 1995-10-23 NZ NZ294191A patent/NZ294191A/xx not_active IP Right Cessation
- 1995-10-23 EP EP95944807A patent/EP0787115B1/fr not_active Expired - Lifetime
- 1995-10-23 PT PT95944807T patent/PT787115E/pt unknown
- 1995-10-23 PL PL95319754A patent/PL184590B1/pl unknown
- 1995-10-23 AU AU36938/95A patent/AU695352B2/en not_active Expired
- 1995-10-23 CN CN95196432A patent/CN1069624C/zh not_active Expired - Lifetime
1997
- 1997-04-10 NO NO19971645A patent/NO313234B1/no not_active IP Right Cessation
- 1997-04-16 FI FI971609A patent/FI114477B/fi not_active IP Right Cessation
- 1997-04-16 BG BG101417A patent/BG62133B1/bg unknown
- 1997-04-18 US US08/839,350 patent/US6043359A/en not_active Expired - Lifetime
- 1997-04-18 NO NO971796A patent/NO971796L/no unknown
- 1997-04-21 MX MX9702892A patent/MX9702892A/es unknown
1998
- 1998-03-31 GR GR980300015T patent/GR980300015T1/el unknown
2000
- 2000-03-15 GR GR20000400665T patent/GR3032965T3/el unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU785385B2 (en) *	2000-03-31	2007-03-29	Sanochemia Pharmazeutika Aktiengesellschaft	Novel derivatives and analogues of galanthamin

Also Published As

Publication number	Publication date
EP0787115A1 (fr)	1997-08-06
CA2203183C (fr)	2008-04-08
DK0787115T3 (da)	2000-05-08
JPH10507457A (ja)	1998-07-21
AU3693895A (en)	1996-05-15
SK283877B6 (sk)	2004-04-06
DE59507585D1 (de)	2000-02-10
ATE188460T1 (de)	2000-01-15
FI114477B (fi)	2004-10-29
KR100352212B1 (ko)	2003-04-18
AU695352B2 (en)	1998-08-13
NO971796L (no)	1997-05-28
HUT77716A (hu)	1998-07-28
PL184590B1 (pl)	2002-11-29
HU217207B (hu)	1999-12-28
NO971796D0 (no)	1997-04-18
FI971609A0 (fi)	1997-04-16
NO313234B1 (no)	2002-09-02
PL319754A1 (en)	1997-08-18
MX9702892A (es)	1998-07-31
ES2106700T3 (es)	2000-05-16
CN1069624C (zh)	2001-08-15
JP4187786B2 (ja)	2008-11-26
WO1996012692A1 (fr)	1996-05-02
BG101417A (en)	1997-12-30
US6043359A (en)	2000-03-28
BR9509406A (pt)	1998-11-03
SK48397A3 (en)	1997-11-05
CN1170395A (zh)	1998-01-14
EP0787115B1 (fr)	2000-01-05
CZ295528B6 (cs)	2005-08-17
NO971645D0 (no)	1997-04-10
GR3032965T3 (en)	2000-07-31
SI0787115T1 (en)	2000-04-30
CZ119597A3 (en)	1997-08-13
RO118419B1 (ro)	2003-05-30
BG62133B1 (bg)	1999-03-31
FI971609L (fi)	1997-06-02
ES2106700T1 (es)	1997-11-16
NZ294191A (en)	1998-10-28
PT787115E (pt)	2000-05-31
RU2146258C1 (ru)	2000-03-10
NO971645L (no)	1997-05-07
GR980300015T1 (en)	1998-03-31

Legal Events

Date	Code	Title	Description
2002-03-08	EEER	Examination request
2015-12-27	MKEX	Expiry	Effective date: 20151023

Publication	Publication Date	Title
CA2203183A1 (fr)	1996-05-02	Procede de preparation de derives de 4a,5,9,10,11,12,-hexahydro-6h-benzofuro[3a,3,2-ef][2]benzazepine
WO2003008479A1 (fr)	2003-01-30	Catalyseur destine a la production de polyester et procede de production de polyester faisant intervenir ce catalyseur
CA2417691A1 (fr)	2002-12-12	Procede de production de l'acide terephtalique purifie
EP1422214A4 (fr)	2007-07-11	Procede de production d'acide dicarboxylique aromatique
CA2151256A1 (fr)	1994-07-21	Production de tetrahydro-isohumulates sans-odeur
CA2247467A1 (fr)	1996-08-29	Utilisation de la piperine pour augmenter la biodisponibilite
EP0405864A3 (en)	1992-01-08	Phospholipase a2 inhibitor, microorganisms producing said inhibitor and processes for its production
CA2361701A1 (fr)	2000-08-10	Procede microbien pour la preparation de la pravastatine
Ramage et al.	1991	Dioxalanones as synthetic intermediates. Part 6. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 2-keto-3-deoxy-D-gluconic acid (KDG)
EP0895985A3 (fr)	2000-10-25	Procédé pour la préparation de composés Bis(amino-3-hydroxy-4-phényl)
AU2596388A (en)	1989-06-01	A process for the synthesis of amikacin
EP0092286B1 (fr)	1987-04-08	Procédé de préparation du 1,1-dioxyde de l'acide pénicillanique et ses dérivés
WO1995034194A3 (fr)	1996-03-07	Procede de production d'un sel d'acide clavulanique
CA2215251A1 (fr)	1999-04-01	Preparation industrielle d'acide gallique de haute purete
EP0983999B8 (fr)	2005-06-08	Procede de production de derives amides et de leurs intermediaires
AU1271500A (en)	2000-06-05	High purity production of l-ribose from l-arabinose
CA2146708A1 (fr)	1995-10-19	Methode de preparation de derives de la glutamine
WO2005063731A3 (fr)	2005-11-17	Production de dihydronepetalactone par reduction de l'acide nepetalique
CA2322231A1 (fr)	2001-04-05	Procede de purification de la s-adenosyl-l-methionine et de preparation de sels de ce compose convenant a des applications pharmaceutiques
IL157312A0 (en)	2004-02-19	Processes for the preparation of epothilone derivatives and compounds produced thereby
CA2227131A1 (fr)	1998-07-22	Methodes pour la preparation de derives de la benzophenone
US6197955B1 (en)	2001-03-06	Production of staurosporine derivative using acid isomerization
EP1031565A4 (fr)	2001-01-31	Nouveau cristal de derive depsipeptidique et procede de production
GR3021889T3 (en)	1997-03-31	Diacetyl production
EP0267605A3 (fr)	1990-06-20	Composés intermédiaires dans un procédé de préparation de dérivés de l'acide 16-phénoxy et 16-phénoxy substitué-prostatriénoiques

CA2203183A1 - Procede de preparation de derives de 4a,5,9,10,11,12,-hexahydro-6h-benzofuro[3a,3,2-ef][2]benzazepine - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (5)

Publications (2)

Family

ID=25597335

Family Applications (1)

Country Status (27)

Cited By (1)

Families Citing this family (28)

Family Cites Families (5)

Cited By (1)

Also Published As

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